The present invention relates to androstane 17.alpha.-hydroxy-17.beta.-carbothioic acids and to processes for the preparation thereof. The compounds of the invention are intermediates, primarily of use in preparing anti-inflammatory androstane 17.beta.-carbothioate esters.
Anti-inflammatory steroids are most typically of the corticoid type, i.e. in the pregnane series. Certain androstane compounds containing a variety of carbothioate groupings in the 17.beta.-position have been found to possess anti-inflammatory properties. In particular such androstane compounds are described and claimed in U.S. patent application Ser. No. 234,113 filed by G. H. Phillipps, B. M. Bain, C. Williamson, I. P. Steeples and S. B. Laing on Feb. 13, 1981.
In general, these anti-inflammatory androstane 17.beta.-carbothioates have the partial formula ##STR2## where R.sup.a represents a C.sub.1-6 alkyl group, a C.sub.1-2 alkyl group carrying a terminal halogen atom, or a benzyl group which may be substituted by a C.sub.1-4 alkyl or C.sub.1-4 alkoxy group or a halogen atom; and OR.sup.b represents a group --OCOR.sup.d, where R.sup.d represents a hydrogen atom or a C.sub.1-5 alkyl group and R.sup.c represents a hydrogen atom or a methyl group (in either the .alpha.- or .beta.-configuration) or a methylene group or OR.sup.b and R.sup.c together represent a 16.alpha., 17.alpha.-isopropylidenedioxy group. They may be generally represented by the formula:- ##STR3## wherein R.sup.a, R.sup.b and R.sup.c are as previously defined; R.sup.e represents a hydrogen, fluorine or chlorine atom in either the .alpha.- or .beta.-configuration; R.sup.f represents a hydrogen, fluorine, chlorine or bromine atom; R.sup.g represents a hydrogen, fluorine, or chlorine atom; R.sup.h represents a hydroxy group in the .beta.-configuration or a keto group or, when R.sup.g represents a chlorine atom, a chlorine or fluorine atom in the .beta.-configuration; R.sup.i represents a hydrogen atom or where a 1,2-double bond is present, optionally a chlorine or bromine atom and the symbol represents a single or double bond.